10 Most Beautiful Cities in Sicily

Sicily served as the center of the universe to the ancient world. The beautiful island has a violent history of empires rising and falling, leaving a layered cultural tapestry that you could spend a lifetime unraveling. In fact, the island is still being violently kicked, in a way. It sits at the toe-end of Italy’s swinging boot on a map. An overview of the most amazing cities in Sicily:

1. Trapani

A Baroque architecture paradise, Trapani hugs the northwestern-most tip of Sicily. The city rises around the harbor where Peter of Aragon originally landed in 1282 to begin the Spanish occupation of the province. In the old town, you can still see the remnants of Trapani’s robust trading network that once spanned from Venice to Carthage. Fish, salt and wine were the city’s powerful vehicles of commerce. Now the harbor and half-moon shaped old town are frequented by boat travelers awaiting ferries to Egadi Islands and Pantelleria.

2. Agrigento

The Greek city of Akragas once protected over 800,000 people during the golden age of Ancient Greece. Now it is the sight of historic Agrigento in the south of Sicily. At first glance, the city is not very inviting — modern highways and choking traffic put off travelers — but dig a little deeper to find a medieval gem. Via Atenea, in the heart of the city, bustles with restaurants, shops and bars while being crowned by mansions. And just down the hill from Agrigento stands the Valley of Temples, one of the world’s best example of ancient Greek architecture and art.

3. Ragusa

Ragusa crowns a limestone hill surrounded by two deep valleys. At the very top of the hill you’ll find Ragusa Superiore, the grid-patterned modern capital of the Ragusa province. Just below on the slopes of the hill sits Ragusa Ibla, or old town, where ancient alleys carve intricate patterns past gray stone houses and Baroque palazzi. Old town was destroyed in a 1693 earthquake. The residents left the dilapidated ruins to build Ragusa Superiore atop the hill but later resurrected Ragusa Ibla to its former glory. The towns officially merged in 1929.

4. Marsala

You probably know Marsala for super-sweet dessert wines, but it hides a dark history. The ancient Phoenicians escaped the fallen city of Mosia in 397 BC. The Phoenicians vowed never to be defeated and fortified the city with 23-foot thick walls, but the city eventually fell in AD 830 to the Arabs who renamed the city Port of the Gods, or Marsa Allah. Now Marsala is a family-friendly town with marble streets, wine shops, piazzas and Baroque buildings.

5. Syracuse

Syracuse, birthplace and home to the preeminent mathematician Archimedes, was once the largest city in ancient times; bigger than even Athens. The 2,700-year-old city is part of the Bible as the apostle Paul once stayed here. Now the city serves as a shining example of all that is beautiful about the Mediterranean and Sicily. Citrus trees rise through Greek ruins, ancient alleys squiggle down to crystal clear ocean water and Baroque architecture takes the breath away. It’s no wonder Cicero once called Syracuse the greatest and most beautiful ancient Greek city.

6. Erice

Erice sits 2,460 feet above the coastal city of Trapani upon Mount Eryx. In the center of the hilltop town a temple devoted to Venus once stood. Upon the temple is built two castles — the Pepoli Castle and Venus Castle — both dating back to different ancient times. Despite being sacked multiple times, the walled city still holds ruins of the Elymian and Phoenician periods. Modern Erice is home to Sicily’s most famous bakeshop, Maria Grammatico, so come for the pastries and stay for the view.

7. Monreale

The gold of the mosaics gleams through the archways of Monreale’s cathedral. This small, hillside city near Palermo is famous for it’s Norman cathedral. The church was built extravagantly to compete with a cathedral being built in Palermo in the 12th century. William the Good, ruler of Monreale, wanted a lavish place where he and his successive Monreale rulers could be buried. Monreale is connected to Palermo by bus. While many visitors make Monreale a day trip, it’s beautiful views and great food convinces some to extend their stay.

8. Cefalu

Find one of Sicily’s best beaches in the heart of this beautiful northern city. The water is electric blue and crystal clear making the honey-colored Arab-Norman buildings even more breathtaking. And if you can take your eyes off the buildings, you’d gasp at the mountains that crown the city. The pace of living is slow in Cefalu. Wander by the coast and you’ll see throngs of Italian fisherman tending to their boats and discussing the day’s catch. The architecture makes for perfect nighttime strolls through the oceanside promenade or main street. And don’t forget to marvel at the mosaics of the town’s cathedral.

9. Palermo

Palermo, once at the heart of the ancient world, is a diverse city. At the edge of Europe and close to Africa and the Middle East, this city has been conquered and destroyed many times. A handful of cultures have risen and fallen like the Mediterranean waves that lick at the city’s feet. Evidence of this ebb and flow can be seen in the city’s market where exotic spices are sold in the shadows of towering Baroque cathedrals, and where Arab architecture is adorned with Byzantine mosaics. It is home to Italy’s biggest opera house and an array of new, fresh restaurants celebrating the city’s diverse past.

10. Taormina

Taormina is one of Sicily’s unique gems. Perched high on a mountainside near the Mediterranean, this beautiful city was spared the warring past of Sicily’s larger metropolises. It is perfect for people watching as Europe’s rich and famous choose Taormina as a favorite summer destination. The small city is crowded during summer months because of the breathtaking vistas and performances inside the ancient Greek theater. Avoid the crowds while still enjoying good weather in April, May, September or October.